CN101228013B - Method and composition for adhering materials together - Google Patents
Method and composition for adhering materials together Download PDFInfo
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- CN101228013B CN101228013B CN2006800266865A CN200680026686A CN101228013B CN 101228013 B CN101228013 B CN 101228013B CN 2006800266865 A CN2006800266865 A CN 2006800266865A CN 200680026686 A CN200680026686 A CN 200680026686A CN 101228013 B CN101228013 B CN 101228013B
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/0002—Lithographic processes using patterning methods other than those involving the exposure to radiation, e.g. by stamping
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B82—NANOTECHNOLOGY
- B82Y—SPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES
- B82Y10/00—Nanotechnology for information processing, storage or transmission, e.g. quantum computing or single electron logic
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B82—NANOTECHNOLOGY
- B82Y—SPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES
- B82Y40/00—Manufacture or treatment of nanostructures
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/038—Macromolecular compounds which are rendered insoluble or differentially wettable
- G03F7/0388—Macromolecular compounds which are rendered insoluble or differentially wettable with ethylenic or acetylenic bands in the side chains of the photopolymer
Abstract
The present invention provides a method adhering a layer to a substrate that features defining first and second interfaces by having a composition present between the layer and the substrate that forms covalent bonds to the layer and adheres to the substrate employing one or more of covalent bonds, ionic bonds and Van der Waals forces. In this manner, the strength of the adhering force of the layer to the composition is assured to be stronger than the adhering force of the layer to the composition formed from a predetermined adhering mechanism, i.e., an adhering mechanism that does not include covalent bonding. Additionally, the present invention is directed to a composition of adhering together first and second materials. The composition features a multi-functional reactive compound that includes a backbone group and first and second functional groups; a cross-linker, and a catalyst. The first functional group is responsive to a first actinic energy to form cross-linked molecules and to adhere a subset of the cross-linked molecules to the first material. The second functional group is responsive to a second actinic energy, differing from the first actinic energy to adhere to the second material.
Description
About the research of federal funding or the statement of exploitation
U.S. government enjoys paid clear licensing in the present invention, under situation about limiting, have the right the requirement this patent everyone authorize other people licensing with rational condition, described rational condition be according to national standard association (National Institute of Standards) (NIST) clause of the 70NANB4H3012 of ATP ruling institute ruling provide.
Background of invention
The scope of the invention relates generally to the nanoscale manufacturing (nano-fabrication) of structure.More particularly, the present invention relates to a kind of method, this method can be bonded together different materials, and it is applicable to imprint lithography process (imprint lithographic process).
The nanoscale manufacturing relates to the very little structure of manufacturing, for example has the structure of 1 nanometer or above order of magnitude feature.A kind of promising technology that is used for the nanoscale manufacturing is considered to imprint lithography process.The example of imprint lithography process has a detailed description in many documents, as is registered as U.S. Patent application 10/264960, is entitled as the U.S. publication application 2004-0065976 of " Method and a Mold to Arrange Features on a substrate to Replicate Featureshaving Minimal Dimensional Variability "; Be registered as U.S. Patent application 10/264926, be entitled as the U.S. publication application 2004-0065252 of " Method ofForming a Layer on a substrateto Facilitate Fabrication of Metrology Standards "; Be registered as U.S. Patent application 10/235314, be entitled as the U.S. publication application 2004-0046271 of " Method and a Mold toArrange Features on a substrate to Replicate Features having MinimalDimensional Variability "; Above-mentioned patent all transfers assignee of the present invention.
Referring to Fig. 1, the basic principle in the imprint lithography back is to form embossing pattern on substrate, and substrate especially plays etching mask, therefore forms a kind of figure corresponding to described embossing pattern in substrate.The system 10 that is used for forming embossing pattern comprises the platform 11 of carrying substrates 12 on it and has the template 14 of mould 16 have figure to form surface 18 on the mould 16.It can be smooth and/or smooth basically that figure forms surface 18, perhaps can form figure, forms one or more recesses so therein.Template 14 links to each other with imprint head 20, so that template 14 moves.Connect fuid distribution system 22, this system can be communicated with substrate 12 fluids by chosen position, so that on substrate, deposit polymerizable material 24.The source of supply 26 that connects energy 28 makes energy 28 30 transmission along the path.Imprint head 20 and platform 11 are arranged respectively,, make them be in overlaying state, and be arranged in path 30 to adjust mould 16 and substrate 12.Make any one or both in imprint head 20 and the platform 11 change distance between mould 16 and the substrate 12, to determine volume required at they injection polymerizable materials 24 between the two.
Generally before determining volume required between mould 16 and the substrate 12, first polymerizable material 24 is placed on the substrate 12.Yet, also can obtain polymerizable material 24 being injected these volumes after volume required.Volume required be injected into polymerizable material 24 after, energy source of supply 26 produce powers 28, this energy causes that polymerizable material 24 solidifies and/or is crosslinked that the shape of the polymeric material of formation is consistent with the shape of substrate surface 25 and die surface 18.The control of this technology is adjusted by processor 32, is in the data communication state between this processor and platform 11, imprint head 20, fuid distribution system 22 and the energy source of supply 26, according to the computer-readable program operation that is stored in the memory 34.
A key property that accurately forms pattern in polymerizable material is to reduce (if can not prevent) polymeric material to be adhered on the mould, to guarantee simultaneously suitably to be adhered on the substrate.This phenomenon is called preferential release and cohesive.By this way, the pattern that is recorded in the polymeric material just can not deform in the process of peel of mould.Prior art attempts to use on die surface release layer to improve stripping feature.Release layer normally hydrophobic and/or have a low-surface-energy.Release layer is bonded on the mould.Provide release layer can improve stripping feature.This can will reduce to minimum and find out owing to the pattern deformation in the polymeric material of being recorded in that peel of mould causes by it.In this discussion, such release layer is called release layer in advance, promptly be cured to the release layer on the mould.
Another kind attempts to improve the prior art of release property referring to Bender etc., at Multiple Imprinting inUV-based Nanoimprint Lithography:Related Material Issues, MicroelectronicEngeering, 61-62 (2002), the description in the 407-413 page or leaf.Particularly, employing such as Bender contains the mould of release layer and the UV-curable material of handling through fluorine in advance., the UV-curable layer is applied on the substrate, concrete grammar is the UV-curable fluid of spin coating 200 centipoises for this reason, forms the UV-curable layer.The UV-curable layer is rich in fluorin radical, to improve release property.
Therefore, need to improve the preferential release and the cohesive of imprint lithography process mould therefor.
Summary of the invention
The invention provides and a kind of one deck is adhered to on-chip method, feature is by existing a kind of composition to limit first interface and second contact surface between described layer and described substrate, described composition and described layer form covalent bond, and one or more in use covalent bond, ionic bond and the Van der Waals force combine with described substrate.By this way, the bonding intensity of force of guaranteeing described layer and described composition is greater than having described layer of predetermined adhesion mechanism (adhesion mechanism that does not promptly the comprise covalent bonding) bonding force with composition.The invention still further relates to and be used for composition that first material and second material are glued together.The feature of said composition is to comprise: multifunctional reactive compound, this compound comprise the main chain group and first and second functional groups; Crosslinking agent and catalyst.Described first functional group forms corsslinking molecular to the first photochemical energy-sensitive, makes the subclass of described corsslinking molecular link to each other with described first material.Second functional group combines with described second material to the second photochemical energy-sensitive, and the described second photochemical energy is different from the described first photochemical energy.This paper has described these embodiments and other embodiment.
The invention provides and a kind of one deck is adhered to the on-chip method of imprint lithography, described method comprises:
By between described layer and described imprint lithography substrate, existing a kind of composition to limit first interface and second contact surface, described first interface definition is between described layer and described composition, described second contact surface is limited between described imprint lithography substrate and the described composition, described first interface comprises covalent bond, described second contact surface comprises the mechanism that described composition is bonded in described imprint lithography substrate
Wherein, described composition comprises: multifunctional reactive compound, and this compound comprises first and second functional groups; Described first functional group is to the first photochemical energy-sensitive, form corsslinking molecular, the subclass of described corsslinking molecular is linked to each other to form described first interface with described layer, and described second functional group is to the second photochemical energy-sensitive, and the described second photochemical energy is different from the described first photochemical energy to form described second contact surface.
The accompanying drawing summary
Fig. 1 is the plane sketch according to the etching system of prior art;
Fig. 2 is template and the sketch of facing that is arranged on on-chip impression materials according to the present invention;
Fig. 3 is the sketch of facing of template shown in Figure 2 and substrate, shows among the figure that described impression materials forms figure and solidifies on described layer;
Fig. 4 is the sectional view of the template of contact printing material, illustrates to form weak border thin layer between impression materials that solidifies and template;
Fig. 5 is the detail drawing of impression materials drop shown in Figure 2, shows that drop is divided into zone of being rich in surfactant and the zone that lacks surfactant;
Fig. 6 is the detail drawing with the impression materials layer of spin coating technique deposition, shows that this layer is divided into zone of being rich in surfactant and the zone that lacks surfactant;
Fig. 7 is the sectional view of the template that contacts with solidified imprinting material, and impression materials such as Fig. 5 or deposition shown in Figure 6 are formed on the substrate that comprises priming coat;
Fig. 8 is according to one embodiment of the present invention, can be used to form a kind of plane of chemical constitution of component of the composition of the priming coat shown in Fig. 2,3 and 7;
Fig. 9 is according to second embodiment of the present invention, can be used to form a kind of plane of chemical constitution of component of the composition of the priming coat shown in Fig. 2,3 and 7;
Figure 10 is according to the 3rd embodiment of the present invention, can be used to form a kind of plane of chemical constitution of component of the composition of the priming coat shown in Fig. 2,3 and 7;
Figure 11 is according to the 4th embodiment of the present invention, can be used to form a kind of plane of chemical constitution of component of the composition of the priming coat shown in Fig. 2,3 and 7.
Detailed Description Of The Invention
Referring to Fig. 1 and 2, according to the present invention, mould 36 can be used for system 10, and can limit the surperficial (not shown) with essentially smooth or planar shape.Perhaps, mould 36 can comprise the feature structure of being determined by the recess 38 and the projection 40 at many intervals.Described many feature structures have been determined master pattern, and this master pattern forms the basis that will be formed on the pattern on the substrate 42.Substrate 42 can comprise naked wafer or have configuration one or more layers wafer thereon that wherein one deck is shown as priming coat 45.Therefore, the distance ' ' d ' ' between mould 36 and the substrate 42 reduces.Like this, the feature structure on the mould 36 can be impressed into the suitable zone of substrate 42, as is arranged in the impression materials on the part that presents the substantially flat profile on the surface 44.Should be appreciated that impression materials can adopt any known technology deposition, for example spin coating, dip-coating etc.But in this example, impression materials is deposited on the substrate 42 with the form of the discrete droplets 46 at many intervals.Impression materials can be formed by composition, and selective polymerisation and crosslinked can take place said composition, to write down master pattern therein, limits the pattern of record.
Particularly, the pattern that is recorded in the impression materials is that part is by producing with for example electric interaction of the interaction of mould 36, magnetic interaction, thermal interaction, mechanical interaction etc.In this example, mould 36 contacts with impression materials machinery, with drop 36 drawouts, produces the organizator 50 of the connection of impression materials on surface 44.In one embodiment, reduce distance ' ' d ' ', make the subdivision 52 of impression materials enter and fill recess 38.In order to promote to fill recess 38, with before drop 46 contacts, the atmosphere between mould 36 and the drop 46 is saturated by helium at mould 36, perhaps find time fully, or the part helium atmosphere of finding time.
Impression materials has necessary character, makes it complete filling recess 38, uses the organizator covering surfaces 44 of the connection of impression materials simultaneously.In the present embodiment, when reach required, usually also be minimum range " d " after, impression materials keeps with the subdivisions 54 of projection 40 stacks.This organizator 50 that act as provides thickness t
1Subdivision 52 and thickness t
2Subdivision 54.Thickness " t
1" and " t
2" can be any required thickness, specifically depend on application.Then, be subjected to proper curing agents by making organizator 50, the effect of for example photochemical energy (as broadband uv energy, heat energy etc., depending on impression materials) is solidified organizator 50.This can cause impression materials polymerization and crosslinked.Whole process can be carried out under environment temperature and pressure, perhaps carries out in the environment controlled chamber with temperature required and pressure.After this manner, after organizator 50 solidified, its side 56 had the corresponding to shape of shape with the surface 58 of mould 36.
Referring to Fig. 1,2 and 3, from the formation graphics art of the uniqueness that adopted, the characteristic of impression materials is important for making substrate 42 form figure effectively.For example, need impression materials to have some characteristic, so that fill the feature structure of mould 36 fast and equably, all like this thickness t
1Basically consistent, and all thickness t
2Basically consistent.For this reason, need determine the viscosity of impression materials, to obtain afore-mentioned characteristics according to used depositing operation.As mentioned above, impression materials can adopt various deposition techniques on substrate 42.If impression materials is deposited as the drop 46 at many discrete intervals, the composition that then requires to form impression materials has lower viscosity, for example between 0.5-20 centipoise (cP).Consider that impression materials sprawls and form figure simultaneously, subsequently by radiation with the pattern cured adult 50 that is shaped, require the composition can moistening substrate 42 and/or the surface of mould 36, and avoid after polymerization, then forming hole or hole.If deposit impression materials with spin coating technique, then require to use the higher material of viscosity, for example viscosity is generally hundreds of to thousands of centipoises greater than 10 centipoises, and described viscosimetric analysis is carried out under not solvent-laden situation.
Except afore-mentioned characteristics (being called liquid phase characteristics), also need composition to give impression materials some solidified phase characteristics.For example, after organizator 50 solidified, impression materials need have preferential adhesion and stripping feature.Particularly, the composition of preparation impression materials will help to provide with the preferential adhesion of substrate 42 with to the preferential release of mould 36 for organizator 50.Like this, by peel of mould 36 cause especially because the tearing, stretch or other structural destructions etc. and the possibility that causes the pattern of record to deform will reduce of organizator 50.
Formation provides the composition component of composition of the impression materials of afore-mentioned characteristics can be different, and this is to be formed by many different materials because of substrate 42.As a result, the chemical composition on surface 44 is along with the changes in material that forms substrate 42.For example, substrate 42 can be formed by silicon, plastics, GaAs, tellurium mercury and composite thereof.As mentioned above, substrate 42 can comprise one or more layers (being shown as priming coat 45 among the figure), for example dielectric layer, metal level, semiconductor layer, complanation layer etc., and organizator 50 forms on these layers.For this reason, priming coat 45 can use any suitable technique to be deposited on the wafer 47, for example chemical vapour deposition (CVD), spin-coating method etc.In addition, priming coat 45 can be formed by any suitable material such as silicon, gallium etc.In addition, mould 36 can be formed by some materials, for example pyrogenic silica, quartz, tin indium oxide diamond-like-carbon, MoSi, colloidal sol-gel etc.
The exemplary body material that is used for forming organizator 50 is as follows:
The main body impression materials
Isobornyl acrylate
The just own ester of acrylic acid
Ethylene glycol diacrylate
2-hydroxy-2-methyl-1-phenyl-1-acetone
Acrylate component, promptly isobornyl acrylate (IBOA) has following structure:
It accounts for 47% of material of main part weight, but its content can (contain end value) in the 20%-80% scope.As a result, the mechanical performance of organizator 50 is mainly caused by IBOA.The product of the SR by name 506 of Sa Tuomo (Sartomer) company that the exemplary source of IBOA is Pennsylvania, America Ai Kesidun (Exton).
The just own ester of part acrylic (n-HA) has following structure:
It accounts for 25% of material of main part weight, but its content can (contain end value) in the 0%-50% scope.N-HA both provided flexible for organizator 50, also was used for reducing the viscosity of the material of main part of prior art, made the viscosity of bulk material (contain end value) in the scope of 2-9 centipoise.An exemplary source of n-HA component is the auspicious strange chemical company of Alder (Aldrich Chemical) of University of Wisconsin-Madison Xin Zhou Milwaukee.
The linked ethylene glycol diacrylate has following structure:
It accounts for 25% of material of main part weight, and its content can (contain end value) in the 10%-50% scope.EGDA also influences the formation of modulus and rigidity, and helps in the polymerization process of material of main part that n-HA and IBOA's is crosslinked.
Initiator component 2-hydroxy-2-methyl-1-phenyl-1-acetone can trade name Da Luoke (DAROCUR)
1173 from buying in the Sheba speciality chemical company (CibaSpecialty Chemicals) of the special Rui Zhen of New York, United States (Tarrytown), and it has following structure:
It accounts for 3% of material of main part weight, and its content also can (contain end value) in the 1%-5% scope.Make that initator is the broadband uv energy that medium pressure mercury lamp produces to the photochemical energy of its sensitivity.By this way, initator promotes the crosslinked and polymerization of component of material of main part.
But, with Frank Xu and Michael N.Miller classify as the inventor, the Application No. 11/068 that is entitled as pending trial in " reducing the fusible composition (Composition to ReduceAdhesion Between a Conformable Region and a Mold) between uniformity zone and the mould " submitted on February 28th, 2005, in 171, having disclosed required preferential adhesion discussed above and release property can be by forming weak boundary layer as shown in Figure 3 and Figure 4 between mould 36, surface 58 and organizator 50, thin layer 60 and obtaining.After impression materials solidified, thin layer 60 was kept.Therefore, the bonding force between mould 36 and the organizator 50 is very little.For this reason, it is useful finding to use the composition that comprises one of several compositions to be used for impression materials, for example above-mentioned main body impression materials (BULK IMPRINTING MATERIAL), and the component that comprises the low-surface-energy group, these components are called as surface active agent composition, with Frank Xu and Michael N.Miller classify as the inventor, the Application No. of submitting on February 28th, 2,005 11/068 that is entitled as pending trial in " reducing the fusible composition (Composition to Reduce Adhesion Between a ConformableRegion and a Mold) between uniformity zone and the mould ", describe in detail in 171, the document is incorporated into this by reference.
Referring to Fig. 5, after the deposition impression materials, surface active agent composition rises, and after a period of time, rises to air-liquid surface, and the drop 146 of the impression materials with material bifurcated concentration is provided.In first, drop 146 comprises that concentration is higher than the surface active agent composition of second portion, and this component is called and is rich in surface active agent composition (SCR) subdivision 136, and second portion is called and lacks surface active agent composition (SCD) subdivision 137.SCD subdivision 137 is between surface 44 and SCR subdivision 136.In case impression materials solidifies, SCR subdivision 136 can weaken the bonding force between mould 36 and the impression materials.Particularly, surface active agent composition has different two ends.When impression materials is in liquid phase, promptly during polymerizable, one of different two ends have compatibility to being included in the material of main part that comprises in the impression materials.The other end has fluorine component.
Referring to Fig. 4 and Fig. 5, owing to compatibility to material of main part, the surface component orientation, so fluorine component is stretched out from the air-liquid surface that is limited by impression materials and surrounding environment.
When impression materials solidifies, first's impression materials formation thin layer 60 ', the second portion impression materials, the polymeric material that promptly is shown as organizator 50 solidifies.Thin layer 60 is between organizator 50 and mould 36.Thin layer 60 is to form owing to fluorine component is present in and is positioned at SCR subdivision 136.Thin layer 60 prevents to form between mould 36 and the organizator 50 strong bonding force.Particularly, organizator 50 has relative first 62 and second 64.Face 62 is adhered on the mould 36 with first bonding force, and face 64 is adhered on the substrate 42 with second bonding force.Thin layer 60 causes first bonding force less than second bonding force.As a result, mould 36 removes from organizator 50 easily, will be out of shape simultaneously and/or peel of mould 36 required power reduce to minimum.Though the organizator 50 that illustrates has the face 62 that is formed figure, not smooth even should be appreciated that face 62, also can be smooth.
In addition, if need, can between organizator 50 and substrate 42, form thin layer 60.For example, can be by on mould 36, applying impression materials, substrate 42 is contacted with impression materials on mould 36 realize this point.Like this, we can say that organizator 50 will be positioned at thin layer 60 and main body, for example between mould 36 or the substrate 42, on this mould 36 or substrate 42, deposit polymerizable material.Should be appreciated that bifurcated concentration can appear in material similarly, as shown in Figure 6 SCR subdivision 236 and SCD subdivision 237 if adopt spin coating technique deposition impression materials.The differentiation required time depends on a number of factors, and comprises the molecular size in the composition and the viscosity of composition.When the viscosity of composition was lower than 20 centipoises, composition concentration above-mentioned differentiation required time occurred and only is the several seconds.But when the viscosity of material is hundreds of centipoise, may need several seconds to time of several minutes.
But have been found that described thin layer 60 may not be uniform.Some zones of thin layer 60 are regional thinner than other, under some extreme cases, may not have thin layer 60 in the minimum percentage range of template surface, so template 36 contact with organizator 50.Thin layer 60 has thin zone and does not exist the result of thin layer 60 to be, the distortion of organizator 50 may take place and/or from substrate 42 delaminations.Specifically, in peel of mould 36, organizator 50 is subjected to separation force F
SSeparation force F
SBe owing to the tensile force f that is applied on the mould 36
P, and organizator 50 that reduces to cause owing to thin layer 60 and the bonding force between the mould 36, for example Van der Waals force produces.Since the existence of thin layer 60, separation force F
SSize usually less than the bonding force F between organizator 50 and the substrate 42
ASize.But, by reducing or not having a thin layer 60, local separation force F
SCan be near local bonding force F
ASize.By-local forces what is illustrated in the active force that the specific region of thin layer 60 exists, and it be near the by-local forces what in or the non-existent substantially zone of thin layer 60, the very thin zone of thin layer 60 in this example.This causes organizator 50 distortion and/or from substrate 42 delaminations.
For Fig. 7, under the situation that has priming coat 45, owing to have two interfaces 66 and 68, it is more complicated that situation becomes.At 66 places, first interface, between priming coat 45 and organizator 50, there is the first bonding force F
1At second contact surface 68, between priming coat 45 and wafer 47, there is the second bonding force F
2Need separation force F
SSize less than adhesive effect power F
1And F
2Yet, because there are not separation force F in thin layer 60 varied in thickness as discussed above or thin layer 60
SMay be similar or near bonding force F
1And F
2In one or two size.This may cause organizator 50 from priming coat 45 delaminations, and priming coat 45 is from wafer 47 delaminations, and perhaps two kinds of situations all have.
The present invention even can not avoid above-mentioned delamination problems, also can reduce this problem by forming priming coat 45 by a kind of material, because the thin layer fluctuating, described material makes the F at first and second interfaces
1And F
2Bonding force is respectively greater than separation force F
3Possibility increase.Therefore, priming coat 45 is by at interface 66 (promptly between priming coat 45 and organizator 50), and forms strong bonding composition form between interface 66, priming coat 45 and wafer 47.In this example, bonding between first interface, 66 place's priming coats 45 and organizator 50 is the result of covalent bonding, promptly is being used for forming the composition of priming coat 45 and is being used for forming between the composition of organizator 50 and has covalent bond.Bonding can the realization between described priming coat 45 and the wafer 47 by in the various mechanism any one.These mechanism can comprise and are used for forming the composition of priming coat 45 and are used for forming between the material of wafer 47 and form covalent bond.Covalent bond or except that covalent bond as an alternative can be used for forming the composition of priming coat 45 and be used for forming between the material of wafer 47 and form ionic bond.Covalent bond and/or ionic bond or both as an alternative, or except that covalent bond and/or ionic bond or both are used for forming the composition of priming coat 45 and are used for forming bonding can the realization by mutual Van der Waals force between the material of wafer 47.
This is to finish by forming priming coat 45 by the composition that comprises multifunctional reactive compound, and described multifunctional reactive compound is the compound that comprises two or more functional groups that following general formula is represented:
(1)X′——R——X
R in the formula, R ', R " and R
Be linking group, x, y, z are the average repeat numbers of the group that is attached thereto.These repetitives can be random distribution.Radicals X and X ' expression functional group are generally understood as the X of functional group and are different from the X ' of functional group.A kind of among X of functional group and the X ', for example X ' selects, to finish and to be used for forming the cross-linking reaction of the material of substrate 42, so that by combining with it with its formation covalent bond, ionic bond and/or Van der Waals force.
A kind of among remaining X of functional group and the X ', for example X selects, and finishing and to be used for forming the cross-linking reaction of the material of organizator 50, thereby forms covalent bond between them.Determine the degree of functionality of X group, so that in the polymerization process of organizator 50, take place crosslinked.Therefore, the properties of materials that is used for forming organizator 50 is depended in the selection of the X of functional group, need the X of functional group can with the functional group reactions of the composition that is used for forming organizator 50.For example, if organizator 50 is formed by acrylate monomer, then X can be by acrylic functional group, vinethene functional group or alkoxy-functional, and/or can form with the functional group of acrylic groups copolymerization in the organizator 50.Therefore, X functional group responds to the ultraviolet photochemical energy, and cross-linking reaction takes place.
The X ' of functional group also can participate in the crosslinked and polymerisation of priming coat 45.Usually, X ' functional group responds to a kind of photochemical energy (this energy is different from the photochemical energy that X functional group cross-linking reaction is responded), promotes polymerization and cross-linking reaction.X ' functional group in this example responds for suffered heat energy, promotes molecule crosslinked in the priming coat 45.Usually, the X ' of functional group is selected, to promote the cross-linking reaction with substrate 42 by following three kinds of mechanism: 1) directly with the material reaction that is used for forming substrate 42; 2) with the cross-linker molecules reaction that is connected functional group with the crosslinking agent that reacts with substrate 42; Therefore 3) priming coat 45 polymerizations and crosslinked can form the strand of sufficient length, are connected between organizator 50 and the substrate 42.
Referring to Fig. 7 and Fig. 8, the exemplary multifunctional reactive compound that can be used to form priming coat 45 in the presence of the organizator 50 that is formed by material of main part comprises senecioate-carboxyl ethyl ester, it can be available from the UCB chemical company (UCB Chemicals) of State of Georgia, US Shi Maina (Smyrna), and product is called β-CEA.β-CEA is the aliphatic compounds with following structure:
X ' functional group 70 provides carboxyl functional group.X functional group 72 provides acrylate-functional groups.Functional group 70 links to each other with the different ends of backbone component 74 with 72.
Referring to Fig. 7 and Fig. 9, another kind can be used to form priming coat 45 in the presence of the organizator 50 that is formed by material of main part multifunctional reactive compound comprises the aromatic bisphenols compound, it can be available from the UCB chemical company (UCB Chemicals) of State of Georgia, US Shi Maina (Smyrna), product that by name Bi Kerui 3605 (Ebecryl 3605), it has following structure:
X ' functional group 76 provides epoxy-functional.X functional group 78 provides acrylate-functional groups.Functional group 76 and 78 is connected the different ends of backbone component 80.
Referring to Fig. 7 and Figure 10, another kind can be used to form priming coat 45 in the presence of the organizator 50 that is formed by material of main part multifunctional reactive compound comprises aromatic compounds, it can be available from this internal medicine Ta Di international corporation of section (Schenectady InternationalInc.) of this section's internal medicine tower enlightening (Schenectady) of New York, United States, its product is called isorad 501 (Isorad 501), has following structure:
X and y are the integers of the repetitive of expression random distribution in the formula.X ' functional group 82 provides carboxylic functionality.X functional group 84 provides acrylate functionalities.Functional group 82 is connected with the different ends of backbone component 86 with 84.
Referring to Fig. 7 and Figure 11, except taking place the cross-linking reactions with organizator 50, the X of functional group can produce free radical, and described free radical can promote its polymerization at the composition setting up period that is used for forming organizator 50.Therefore, the described X of functional group will promote its polymerization when organizator 50 is subjected to photochemical energy (for example broadband ultraviolet energy) irradiation.An exemplary multifunctional reactive compound that comprises these character is the light trigger available from the Sheba speciality chemical company (Ciba Specialty Chemicals) of the special Rui Zhen of New York, United States (Tarrytown), its commodity are called her and add Cole 2959 (Igacure 2959), have following structure:
X ' functional group 90 provides hydroxy functionality.X functional group 92 provides the degree of functionality of class of initiators.Specifically, can respond by irradiation to being subjected to the broadband ultraviolet, α-cracking takes place in the X of functional group, produces benzoyl type free base.Described free radical promotes to be used for to form the radical polymerization of the composition of organizator 50.Functional group 90 is connected with the different ends of backbone component 94 with 92.
Formed several compositions, it comprises the multifunctional reactive compound that some are above-mentioned, to determine the bonding strength of interface 66 and 68.Be the exemplary composition that comprises multifunctional reactive compound below:
Composition 1
β-CEA
DUV30J-16
Wherein DUV30J-16 has 100 grams approximately in composition 1, and β-CEA has 0.219 gram approximately.DUV30J-16 is the bottom antireflection coatings, BARC, and available from the brewer scientific company (Brewer Science) of Missouri, USA roller (Rolla), it comprises 93% solvent and 7% non-solvent active component.DUV30J-16 comprises phenolic resins, and its crosslinking agent can react with carboxylic acid functional.Think that DUV30J-16 can not form covalent bond with organizator 50.In another composition, β-CEA replaces with crosslinking agent, catalyst and isorad 501.Crosslinking agent and catalyst be all available from N.J., and the Seat of western Paterson (West Patterson) gram Industrial Co., Ltd (Cytec Industries, Inc.).The product of described crosslinking agent is called Sai Maier 303ULF (Cymel303ULF).A kind of key component of Sai Maier 303ULF is hexamethoxy methyl-melamine (HMMM).The methoxy functional group of described HMMM can participate in many condensation reactions.The product of catalyst is called Sai Kaite 4040 (Cycat 4040), and following composition is provided:
DUV30J-16
Isorad 501
Sai Maier 303ULF
Match Kate 4040
100 gram DUV30J-16 are arranged in the composition 2 approximately, 0.611 gram isorad 501,0.175 Ke Saimaier 303ULF and 0.008 gram match Kate 4040 are arranged in the composition 2.
The composition that another kind can be used as multifunctional reactive compound has saved DUV30J-16.Said composition is as follows:
Isorad 501
Sai Maier 303ULF
Match Kate (Cycat)
PM acetic acid esters (PM Acetate)
The 4th kind of composition is identical with composition 3, and its difference is, constitutes components contents.For example, composition 4 comprises about 85.2 gram isorad 501,13.8 Ke Saimaier 303ULF and 1 gram match Kate 4040.With isorad 501, Sai Maier 303ULF and Sai Kaite mix.With isorad 501, the mixture of Sai Maier 303ULF and Sai Kaite adds in about 1900 gram PM acetic acid esters then.
The 5th kind of composition is identical with composition 3, and difference is to constitute components contents.For example, composition 5 comprises about 81 gram isorad 501,18 Ke Saimaier 303ULF and 1 gram match Kate 4040.With isorad 501, Sai Maier 303ULF and Sai Kaite mix.With isorad 501, the mixture of Sai Maier 303ULF and Sai Kaite adds in about 1900 gram PM acetic acid esters then.
Use spin coating technique, top five kinds of compositions, the composition 1-5 that discusses about priming coat 45 is deposited on the substrate 42 separately, substrate is with the rotation of 500-4000 rev/min speed during deposition, has level and smooth substantially (if not the plane) layer of uniform thickness with formation.Then with 180 ℃ (degree centigrade) hot photochemical energy about 2 minutes to said composition irradiation.
Five kinds of above-mentioned compositions, composition 1-5, use with impression materials, be used for producing the comparing data of the bonding force intensity of interface 66 and 68, be used for comparing with the baseline that records on the priming coat 45 that is formed by DUV30J-16 fully, people do not know that the latter can form covalent bond with the organizator 50 that is formed by impression materials.Therefore, the organizator 50 that will form by the main body impression materials, and be deposited between two slide (not shown)s by the priming coat 45 that composition 1-5 and baseline composition form, solidify then.The thickness of each slide (not shown) is about 1 millimeter, and lateral dimension is 75 * 25 millimeters.
Before deposition of primer layer 45 and organizator 50, the slide (not shown) is cleaned.Specifically, make each slide (not shown) and skin so breathe out (Piranha) solution (H
2SO
4: H
2O
2(volume ratio)=2.5: 1) contact.Use deionized water drip washing slide (not shown) then, sprayed with isopropyl alcohol, contacting with fluid stream (for example nitrogen stream) carries out drying then.The slide (not shown) was toasted 2 hours down at 120 ℃ then.
Use spin coating technique that priming coat 45 is deposited on each sheet (not shown) of two slides, rotating speed is up to 3000rpm.Heated 2 minutes on 180 ℃ of electric hot plates at the priming coat on the slide (not shown) 45.In other words, composition 1-5, and baseline composition solidifies by the effect that is subjected to heat energy separately, i.e. polymerization is also crosslinked.Use above-mentioned liquid droplet distribution technology to obtain organizator.Specifically, on the priming coat 45 that the main body impression materials one of is arranged in two slides with the form of many drops.By the priming coat on two slide (not shown)s is faced mutually, contact main body impression materials is clipped in the main body impression materials between two priming coats 45 then.Usually in described two slide (not shown)s the longitudinal axis of a slice along extending with the direction of the longitudinal axis quadrature of remaining slide (not shown).Press in the use ultraviolet mercury lamp to these two slide irradiation intensities be 20 milliwatts/centimetre
2Photochemical energy (for example broadband ultraviolet wavelength) 40 seconds, make the main body impression materials solidify, i.e. polymerization is also crosslinked.
In order to measure bonding intensity, use four-point bending anchor clamps (not shown) to carry out the description " Measurement of Adhesive Force Between Mold andPhotocurable Resin in Imprint Technology " that this measuring method of bonding test is similar to following document, Japanese Journal of Applied Physics, the 41st volume, (2002), 4194-4197 page or leaf.Get maximum force/load as adhesion value.2 crossbeam (beam) distance is 60 millimeters up and down.Speed with 0.5 mm/min applies load.Use this test to record, when priming coat 45 is formed by baseline composition, issue layer estranged at 6.1 pounds active forces.When priming coat 45 was formed by composition 1, the separation force that reached before layering occurring was about 6.5 pounds.When priming coat 45 was formed by composition 2, the separation force that reached before layering occurring was about 9.1 pounds.When priming coat 45 was formed by composition 3,4 or 5, before layering occurring, a slice in two slide (not shown)s or two just damaged (breakage).Therefore, record active force and do not observe layering up to 11 pounds.Therefore, observe composition 3,4 and 5 and provide operating characteristics and good to priming coat 45, because have the undesirable thin zone of people or complete non-existent the time when thin layer 60, this priming coat 45 can prevent layering effectively.
Embodiments of the present invention mentioned above are exemplary.Can when keeping within the scope of the present invention, carry out many changes and improvements.For example, mainly use other formation component of solvent PM acetic acid esters dissolved composition 3,4 and 5.Therefore, many photoresist solvents commonly used can be used to replace the PM acetic acid esters, diethylene glycol monoethyl ether acetate for example, methyl amyl ketone etc.In addition, the solids content in the composition 3,4 and 5 (is benchmark in the composition weight), promptly isorad 501, and the content of Sai Maier 303ULF and Sai Kaite can be 0.1-70 weight %, 0.5-10 weight % more preferably, surplus is by solvent composition.Described composition 3,4 and 5 solid constituent separately can comprise the isorad 501 of 50-99 weight %, the Sai Maier 303ULF of 1-50 weight %, and the Sai Kaite 4040 of 0-10 weight %.Therefore scope of the present invention should not be subjected to restriction described above, and should decide according to appended claims and whole full scope of equivalents thereof.
Claims (20)
1. one kind is adhered to the on-chip method of imprint lithography with one deck, and described method comprises:
By between described layer and described imprint lithography substrate, existing a kind of composition to limit first interface and second contact surface, described first interface definition is between described layer and described composition, described second contact surface is limited between described imprint lithography substrate and the described composition, described first interface comprises covalent bond, described second contact surface comprises the mechanism that described composition is bonded in described imprint lithography substrate
Wherein, described composition comprises: multifunctional reactive compound, and this compound comprises first and second functional groups; Described first functional group is to the first photochemical energy-sensitive, form corsslinking molecular, the subclass of described corsslinking molecular is linked to each other to form described first interface with described layer, and described second functional group is to the second photochemical energy-sensitive, and the described second photochemical energy is different from the described first photochemical energy to form described second contact surface.
2. the method for claim 1 is characterized in that, described mechanism is selected from the one group of mechanism that comprises covalent bond, ionic bond and Van der Waals force.
3. the method for claim 1 is characterized in that, described second contact surface forms by making described composition heat cured.
4. the method for claim 1 is characterized in that, the operation at described qualification first and second interfaces also comprises: solidify described composition, limit cured compositions, form described layer on described cured compositions.
5. the method for claim 1 is characterized in that, first functional group of described multifunctional reactive compound and described layer reaction form described covalent bond, described second functional group and the reaction of described imprint lithography substrate.
6. the method for claim 1, it is characterized in that, described composition also comprises crosslinking agent, wherein, first functional group of described multifunctional reactive compound and described layer reaction, form described covalent bond, a kind of reaction in described second functional group and described imprint lithography substrate and the described crosslinking agent.
7. the method for claim 1 is characterized in that, described multifunctional reactive compound also comprises the main chain group, and described main chain group comprises aromatic structure.
8. the method for claim 1 is characterized in that, described first functional group is by forming with the acrylate-functional groups of the described covalent bond of described layer reaction formation.
9. method as claimed in claim 8 is characterized in that, described multifunctional reactive compound also comprises the main chain group, and described main chain group is selected from one group of group being made up of aliphatic group and aromatic group.
10. be used for composition that first material and second material are glued together in the imprint lithography operation, said composition comprises:
Multifunctional reactive compound, this compound comprise the main chain group and first and second functional groups;
Catalyst, and
Crosslinking agent, described first functional group is to the first photochemical energy-sensitive, form corsslinking molecular, the subclass of described corsslinking molecular is linked to each other in the imprint lithography operation with described first material, described second functional group is to the second photochemical energy-sensitive, combine in the imprint lithography operation with described second material, the described second photochemical energy is different from the described first photochemical energy.
11. composition as claimed in claim 10 is characterized in that, the described first photochemical energy comprises heat energy.
12. composition as claimed in claim 10 is characterized in that, described second photochemically can comprise broadband ultraviolet energy.
14. composition as claimed in claim 10 is characterized in that, described multifunctional reactive compound has following structure:
R ' in the formula, R " and R " ' is a linking group, x, y, z are average repeat numbers.
15. composition as claimed in claim 14 is characterized in that, described linking group R ', and R " and R " ' random distribution is in whole described composition.
16. composition as claimed in claim 10 is characterized in that, described first functional group combines with described first material by the adhesion mechanism that is selected from by following one group of mechanism forming: covalent bond, ionic bond, Van der Waals force.
17. composition as claimed in claim 10 is characterized in that, described crosslinking agent comprises and connects functional group, and described first functional group links to each other with described first material by the connection of described crosslinking agent functional group.
18. composition as claimed in claim 10 is characterized in that, described second functional group is attached thereto by forming covalent bond with described second material.
19. composition as claimed in claim 10 is characterized in that, described first functional group is selected from the one group of functional group that is made up of following: hydroxy-acid group, epoxide group, hydroxyl and alkoxy base.
20. composition as claimed in claim 10 is characterized in that, described second functional group is selected from the one group of functional group that is made up of acrylic groups and vinyl ether group.
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US11/187,407 US8557351B2 (en) | 2005-07-22 | 2005-07-22 | Method for adhering materials together |
US11/187,407 | 2005-07-22 | ||
PCT/US2006/021948 WO2007050133A2 (en) | 2005-07-22 | 2006-06-05 | Method and composition for adhering materials together |
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